157701-32-1

Basic information

• Product Name: diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoyl}-L-glutamate
• Synonyms: diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoyl}-L-glutamate
• CAS NO: 157701-32-1
• Molecular Weight: 672.778
• Mol File: 157701-32-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoyl}-L-glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoyl}-L-glutamate(157701-32-1)
• EPA Substance Registry System: diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoyl}-L-glutamate(157701-32-1)

Safety Data

• Hazardous Substances Data: 157701-32-1(Hazardous Substances Data)

Upstream product

• 106-96-7 propargyl bromide 
• 157701-31-0 diethyl N-{p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoyl}-L-glutamate 
• 174487-97-9 2-methyl-3-(2,2-dimethylpropionyloxymethyl)-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazoline-4,6-dione 
• 157701-35-4 2-Methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one 
• 157701-34-3 5-acetamido-6-cyanoindane 
• 59856-06-3 5-acetamidoindane 
• 157701-33-2 5-acetylamino-6-bromoindane 
• 24425-40-9 indan-5-amine 

Downstream Products

• 238413-07-5 Pentafluorophenyl 4-{N-[(6S)-2,3-dimethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoate 
• 157701-73-0 Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate 
• 164724-29-2 Pentafluorophenyl 4-{N-[(6S)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoate 
• 157701-05-8 N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid 
• 157701-39-8 4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid 
• 174487-71-9 4-{N-[(6R/6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid 
• 157701-04-7 N-(4-{N-[(6RS)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid 

Relevant articles and documents

Chemoenzymatic preparation of the novel antifolate thymidylate synthase inhibitor N-(4-{N-[(65)-2-methyl-4-oxo-3, 4, 7, 8-tetrahydro-6-cydopenta[#]quinazolin-6-yl]-Ar-(prop-2-ynyl)amino}-benzoyl)-L- glutamic acid and its glutamyl cleavage product

5-Aminoindane was converted in six steps to the cyclopenta[g]quinazoline ketone 13. Condensation of 13 with diethyl 4-aminobenzoyl-L-glutamate, followed by in situ reduction, produced the secondary amine 15. W-Propargylation of 15, followed by deprotection, gave the diacid 17 as a mixture of diastereoisomers. Treatment of 17 with the bacterial enzyme carboxypeptidase G2 resulted in removal of the L-glutamic acid residue from (6/J)-17 to give a chromatographically separable mixture of the monoacid 18 and the antifolate 5 [(65)-17], which was assayed as an inhibitor of thymidylate synthase (Kfpp = 3 nM). Treatment of isolated diacid 5 with carboxypeptidase G2 produced the monoacid 19 in ;. 98% enantiomeric excess. The (65) stereochemistry of compound 19 has been established by X-ray crystal structure determination of the amide derivative 24.